The word highwayman is first known to be used in the year 1617;[2] other euphemisms included "knights of the road" and "gentlemen of the road". In the 19th-century, American West highwaymen were known as road agents.[3] In the same time period in Australia, they were known as bushrangers.

Some robbed individually, but others worked in pairs or in small gangs. They often attacked coaches for their lack of protection, including public stagecoaches; the postboys who carried the mail were also frequently held up.[4] The famous demand to "Stand and deliver!" (sometimes in forms such as "Stand and deliver your purse!" "Stand and deliver your money!") was in use from the 17th century.

A fellow of a good Name, but poor Condition, and worse Quality, was Convicted for laying an Embargo on a man whom he met on the Road, by bidding him Stand and Deliver, but to little purpose; for the Traveller had no more Money than a Capuchin, but told him, all the treasure he had was a pound of Tobacco, which he civilly surrendered.

The phrase "Your money or your life!" is mentioned in trial reports from the mid-18th century:

Evidence of John Mawson: "As I was coming home, in company with Mr. Andrews, within two fields of the new road that is by the gate-house of Lord Baltimore, we were met by two men; they attacked us both: the man who attacked me I have never seen since. He clapped a bayonet to my breast, and said, with an oath, Your money, or your life! He had on a soldier's waistcoat and breeches. I put the bayonet aside, and gave him my silver, about three or four shillings."

During the 18th century French rural roads were generally safer from highwaymen than those of England; an advantage credited by the historian Alexis de Tocqueville to the existence of a uniformed and disciplined mounted constabulary known as the Maréchaussée. In England this force was often confused with the regular army and as such cited as an instrument of royal tyranny not to be imitated.[14]

In England, after about 1815, mounted robbers are recorded only rarely. The last recorded robbery by a mounted highwayman occurred in 1831.[15] The decline in highwayman activity occurred during the period in which repeating handguns, notably the pepperbox and the percussion revolver, became increasingly available and affordable to the average citizen. The development of the railways is sometimes cited as a factor, but highwaymen were already obsolete before the railway network was built. A very important factor was the expansion of the system of turnpikes, manned and gated toll-roads, which made it all but impossible for a highwayman to escape notice while making his getaway. At the same time, London was becoming much better policed: in 1805 a body of mounted police began to patrol the districts around the city at night. London was growing rapidly, and some of the most dangerous open spaces near the city, such as Finchley Common, were being covered with buildings. A greater use of banknotes, more traceable than gold coins, also made life more difficult for robbers.[16]Enclosure, and with it the decline in undeveloped open fields and increase in private incentives to regulate trespassers, may also have played a role.

The protocol from the trial with Juraj Jánošík. Jánošík is called here "agili Georgius Janošík Tyarchoviensis latronum et praedorum antesignatus" - cautious (or agile) Juro Jánošík from the Ťarchová, the chief of the thieves and outlaws.

Tradition identifies Saint Dismas, or the Penitent Thief, as a highwayman. Crucified with Jesus Christ, he repented of his sins and was told by Jesus, "This day you shall be with Me, together in paradise."

The bandits in Greece under Ottoman rule were the Klephts (κλέφτες), Greeks who had taken refuge in the inaccessible mountains. The klephts, who acted as a guerilla force, were instrumental in the Greek War of Independence.

The highwaymen of 18th- and 19th-century Kingdom of Hungary were the betyárs. Until the 1830s they were mainly simply regarded as criminals but an increasing public appetite for betyar songs, ballads and stories gradually gave a romantic image to these armed and usually mounted robbers. Several of the betyárs have become legendary figures who in the public mind fought for social justice. The most famous Hungarian betyárs were Sándor Rózsa, Jóska Sobri, Márton Vidróczki, Jóska Savanyú. Slovakia's Juraj Jánošík (Hungarian: György Jánosik) is still regarded as the Slovakian Robin Hood.

The Indian Subcontinent has had a long and colorful history of organised robbery for millennia. Most famous of these were the Thuggees, a quasi-religious group that robbed travellers on Indian roads until the cult was systematically eradicated in the mid-1800s by British colonial administrators. Thugees would befriend large road caravans, gain their confidence, strangle them to death at the right moment, and then rob them of their valuables. According to some estimates the Thuggees murdered 1 million people between 1740 and 1840.[17] More generally, armed bands known colloquially as "dacoits" have long wreaked havoc on many parts of the country. In recent times this has often served as a way to fund various regional and political insurgencies that includes the Maoist Naxalite movement.

The bandits in Serbia, Bosnia and Croatia under Ottoman rule were the Hajduks (Hajduci, Хајдуци), rebels who opposed Ottoman rule and acted as a guerilla force, also instrumental in the many wars against the Ottomans and especially the Serbian revolution. Serbian and Croatian refugees in Austro-Hungarian (and Habsburg) lands were also part of the Uskoci. Notable freedom fighters include Starina Novak, a notable outlaw was Jovo Stanisavljević Čaruga.

From the early 18th century, collections of short stories of highwaymen and other notorious criminals became very popular. The earliest of these is Captain Alexander Smith's Complete History of the Lives and Robberies of the Most Notorious Highwaymen (1714). Some later collections of this type had the words The Newgate Calendar in their titles and this has become a general name for this kind of publication.[20]

There were many broadsheet ballads about highwaymen; these were often written to be sold on the occasion of a famous robber's execution. A number of highwaymen ballads have remained current in oral tradition in England and Ireland.[21]

The traditional Irish song "Whiskey in the Jar" tells the story of an Irish highwayman who robs an army captain, and includes the lines "I first produced me pistol, then I drew me rapier. Said 'Stand and deliver, for you are a bold deceiver'."

The traditional Irish song "The Newry Highwayman" recounts the deeds and death of a highwayman who robbed "the lords and ladies bright". The traditional Irish song "Brennan on the Moor" describes an escapade of the "bold, undaunted robber". Adam and the Ants had a number one song for five weeks in 1981 in the UK with "Stand and Deliver". The video featured Adam Ant as an English highwayman.

The contemporary folk song "On the Road to Fairfax County" by David Massengill, recorded by The Roches and by Joan Baez, recounts a romantic encounter between a highwayman and his female victim. In the end, the highwayman is hanged over the objections of his victim.

In Fable II, Highwaymen appear as an elite type of enemy which works alongside bandits and makes use of speed and agility over brute strength. It is also possible for players to dress as Highwaymen. There is an enemy type in The Elder Scrolls V: Skyrim called the "bandit highwayman" that acts as one of the higher-level bandit enemies. In World of Warcraft one can encounter the Defias Highwaymen, the strongest members of the Defias Brotherhood.

^Brewer, E. Cobham. Dictionary of Phrase and Fable, 1898, defines road-agent as "A highwayman in the mountain districts of North America," citing the generation earlier, W. Hepworth Dixon, New America, p. 14: "Road-agent is the name applied in the mountains to a ruffian who has given up honest work in the store, in the mine, in the ranch, for the perils and profits of the highway."